32 Most Outrageous MTV VMAs Moments of All Time

11. Diana Ross Meets Lil Kim's Cleavage (1999)

Lil Kim made a splash at the 1999 ceremony, with an electric purple wig that matched her much-chattered-about-outfit — a jumpsuit that dipped below her left breast, allowing it to roam free with only a pastie encumbering it. When Diana Ross came out to present Best Hip-Hop Video with Kim and Mary J. Blige, she was so enamored with Kim's willingness to show skin that she skipped the customary, "Hi, how are you" hug and went straight for her co-presenter's cleavage, giving it a jiggle that induced a big laugh from its recipient.